2053424-88-5

Basic information

• Product Name: isopropyl ((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate
• Synonyms: isopropyl ((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate;isopropyl (((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate
• CAS NO: 2053424-88-5
• Molecular Formula: C21H29N6O7P
• Molecular Weight: 508.464721
• EINECS: -0
• Mol File: 2053424-88-5.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 640.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• PKA: 4.21±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: isopropyl ((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: isopropyl ((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate(2053424-88-5)
• EPA Substance Registry System: isopropyl ((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate(2053424-88-5)

Safety Data

• Hazardous Substances Data: 2053424-88-5(Hazardous Substances Data)

Usage

Uses

(R)-isopropyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate is an impurity of Tenofovir (T018500) which is an acyclic phosphonate nucleotide analogue and reverse transcriptase inhibitor. It is used as an anti-HIV agent. Antiviral.

Upstream product

• 147127-20-6 tenofovir 
• 108-95-2 phenol 
• 39613-92-8 (R)-1-isopropoxy-1-oxopropan-2-aminium chloride 
• 379270-35-6 ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoric acid monophenyl ester 
• 79487-89-1 (R)-isopropyl 2-aminopropanoate 
• 101-02-0 triphenyl phosphite 
• 2053424-88-5 (((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alanine isopropyl ester 
• 87-69-4 L-Tartaric acid 
• 39613-92-8 alanine isopropyl ester hydrochloride 
• 39825-33-7 isopropyl L-alanine 
• 66224-66-6 adenine 

Downstream Products

• 379270-37-8 (S)-isopropyl-2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate 
• 1392275-56-7 tenofovir alafenamide hemifumarate 
• 1392275-56-7 tenofovir alafenamide fumarate 

Relevant articles and documents

Method for preparing antiviral drug tenofovir alafenamide fumarate

The invention discloses a method for preparing an antiviral drug tenofovir alafenamide fumarate, which comprises the following steps of: (1) reacting adenine with (R)-propylene carbonate to generate a compound I; (2) treating the compound I with magnesium tert-butoxide, and then adding phosphonate S to react to obtain a compound II; (3) the compound III is obtained by hydrolyzing the compound II in hydrobromic acid; (4) reacting the compound III with thionyl chloride to obtain phosphonyl chloride, and directly reacting the phosphonyl chloride with L-alanine isopropyl ester without purification to generate a compound IV; and (5) obtaining a final product, wherein the preparation of the propionyl phenol fumarate tenofovir is completed by salifying the compound IV and fumaric acid. The method has the advantages of few synthetic route steps, mild reaction conditions and principle saving, and can improve the yield of the final product.

Industrial synthesis method of propofovir disoproxil fumarate

The invention provides a preparation process of propofovir disoproxil fumarate, which is short in production period, simple to operate and suitable for industrial production, and the high-purity propofovir disoproxil fumarate is prepared by taking the propofovir disoproxil fumarate as a starting material through special phosphorus chiral atom synthesis, purification and separation. The purity of the prepared propofovir disoproxil fumarate is greater than 99.90%, the diastereoisomer is less than 0.15%, the content of other single impurities is less than 0.10%, and the method has high commercialscale production value.

Preparation method of tenofovir alafenamide

The invention relates to a preparation method of tenofovir alafenamide represented by a formula IV. The preparation method comprises the following steps: 1) performing a halogenation reaction on a compound I and a halogenation reagent to obtain a halogenated compound II, wherein the halogenated compound II is a raceme; 2) performing solvent-mediated asymmetric transformation on the halogenated compound II obtained in the step 1) in an organic solvent B, and removing the solvent after the complete reaction to obtain a compound III, wherein the asymmetric conversion reaction is carried out at atemperature lower than the reflux temperature of the organic solvent B, a ratio S/R of the two diastereoisomers in the compound III is greater than or equal to 90%, and the organic solvent B is one ora combination comprising one or a plurality of materials selected from toluene, dimethylbenzene, ethylbenzene and chlorobenzene; and (3) carrying out an amidation reaction on the compound III obtained in the step (2) and L-alanine isopropyl ester or a salt thereof to prepare the tenofovir alafenamide represented by the formula IV. The preparation method disclosed by the invention can be used forenhancing the reaction controllability and shortening the reaction time, and is suitable for industrial production of TAF.